'Insecure' Stars Tease What's in Store for Season 5 and an Unexpected Ending (Exclusive)

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Insecure is coming to its end. After five seasons, the Emmy-winning HBO series is kicking off its final season this Sunday -- but there's still a lot of story to tell.

It's all about glowin' up and growin' up for Issa (Issa Rae), who feels stuck in her career and love life after finding out that Lawrence (Jay Ellis) is expecting a baby with his ex, Condola (Christina Elmore). There's also the tension between her and her bestie, Molly (Yvonne Orji), who are both evaluating everything important in their lives.

Rae told ET that the fifth season kicks off three months after the season 4 finale, with Issa "really just focused on trying to figure out how to move forward, if she can move forward, and what she can do with a lot of the things she's built in her business and in her personal life."

Right when things were working out for Issa and Lawrence, Condola's bombshell news puts a halt in their relationship. So how will Lawrence navigate his love for both women?

"That is the journey of this season," Ellis explained. "It is like, What does that really mean when you got your work life in balance and it seems like you have your love life in balance, and then obviously this big shot comes in with the baby, right? And now you are just trying to find sure footing. You are just trying to find somewhere to stand up and not be sinking."

"And I think that is what Lawrence is doing," he continued. "I think he is also realizing, just because he had a vision, it doesn’t have to be the exact way [he envisioned it]. There can be a different route. There can be a different path to that vision and I think that is what this season is all about for him."

Of course, Condola also has to figure out her own future after deciding to keep the baby. Will she be a single mother or learn to co-parent with Lawrence? That is exactly what Elmore said fans will watch play out.

"We are just figuring it out. I think you can tell, the season ended last year, I'm like, 'What's gonna happen?!' And we start to figure that out," she explained. "The baby shook things up, she didn't do nothing."

While Issa handles the baby momma drama, Molly is facing her own hurdles in every aspect of her life.

"She is trying to figure out work, love, friendship. And those are a lot of hurdles right there," Orji detailed. "I mean, listen, is she me? Am I her?"

One thing Orji hopes is that her character finds love after having a string of ill-fated lovers.

"I hope," she teased. "That's all we can do is hope. The struggle has been real and I think one thing that is good about this show is that we don't shy away from the struggles. She hasn't in four seasons."

Showrunner Prentice Penny sums it up as the characters are redefining what happiness means to them this final season.

"Real life gives you a deck of hands, like a card, and then you go, 'How are you going to play those cards?'" he explained. "Last year with Issa [and] Lawrence, happiness is a choice. It's how you define that. So sometimes you can decide that happiness is a feeling, it can change, and so I think that is what we are going to see, is how people redefine happiness."

Issa Rae Yvonne Orji Insecure season 5
Raymond Liu

With 10 new episodes ahead, one has to ask, are they happy with how their characters' storylines wrapped?

"I think so, but I am still gonna be surprised by a little bit of it," Elmore teased, with Orji quipping, "You know our fans are never satisfied, they're never!"

"So even if I say yes, you're going to play this tape back and be like, 'Yvonne said we were gonna be satisfied and we were not and so we have beef,'" she joked. "I don't want no smoke, but at the same time, I was satisfied. I thought Issa did an amazing job writing the finale and sending these characters off on their way."

Penny, meanwhile, added, "I think you are going to get a little bit of both" of a happy ending and life doesn't always turn out how you expect it. However, he knows that Insecure fans "have a high bar for themselves."

"They have a high bar for what they want to see reflected onscreen," he noted. "So I think we are going to get some people who are like, 'Oh I hate this,' and then some people who are like, 'Oh my god, I love it.' I am here for all of it."

Insecure season 5
Raymond Liu

And finally, will Issa come out more confident when it's all said and done, or will she be just as insecure?

"This is a journey of growth. So if Issa's in the same place as she was in season 1 then we failed. So I do think you can count to see an evolved Issa," Rae explained. "We get to finish the story that we set up and not a lot of shows get to do that. So I'm just grateful that we got to end it on our terms."

The fifth and final season of Insecure premieres Sunday, Oct. 24 at 10 p.m. ET/PT on HBO.


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